Intelligence Bolsters Gen. Sheridan's Confidence at Winchester (19 SEP 1864)

Photo By Lori Stewart | “Sheridan’s Final Charge at Winchester” by Thure de Thulstrup, c. 1886 (National Park Service)  

UNITED STATES

09.15.2023

Story by Lori Stewart 

U.S. Army Intelligence Center of Excellence

by Lori S. Stewart, USAICoE Command Historian

19 SEPTEMBER 1864
On 19 September 1864, Union forces under the command of Maj. Gen. Philip H. Sheridan defeated Lt. Gen. Jubal A. Early’s Confederate forces at the Third Battle of Winchester in Virginia. Rarely does a battle hinge on a single piece of information, but General Sheridan confessed that a message he received from Winchester schoolteacher Rebecca Wright on the eve of the battle was the critical piece he needed to ensure his success.

After Early’s attack near the Capital in July, Gen. Ulysses S. Grant combined his forces in Washington, western Maryland, and the Shenandoah Valley into a single department commanded by General Sheridan. Grant ordered Sheridan to end Early and his operations in the vital Shenandoah Valley. Throughout August, Sheridan maneuvered through the valley, attempting to fix Early’s forces. Meanwhile, Grant hoped his own operations around Petersburg would force Gen. Robert E. Lee to recall some of the forces reinforcing Early.

By mid-September, Sheridan was at Clifton about six miles from the town of Winchester. Early had his forces deployed on the west bank of the Opequon River east of the town. Encouraged to launch an attack on the Confederates, Sheridan remained concerned about the location of two
divisions, including Maj. Gen. Joseph B. Kershaw’s, that Lee had sent to reinforce Early the previous month. While Sheridan’s forces had captured prisoners from Kershaw’s division, rumors had the enemy unit in Petersburg on 6 September. Sheridan reported he planned, “to take all the time necessary to equip myself with the fullest information and then seize an opportunity under such conditions that I could not …fail.” On 16 September, Sheridan received the critical piece of information he needed for success.

In his official report about the Shenandoah campaign, Sheridan obliquely referred to “reliable information” he received on the eve of the battle. His memoirs published twenty years after the war provided an expanded account. Earlier in August, Sheridan’s “grave apprehension” about the damage “doubtful citizens and Confederate deserters” could do to his army led him to form a battalion of scouts under Maj. Henry K. Young. Often clothed in Confederate uniforms, Young’s scouts monitored Early’s movements in the valley. Near Winchester, they met Thomas Laws, an elderly black man loyal to the Union who, under a Confederate permit, traveled into town to sell vegetables. Brig. Gen. George R. Crook, a corps commander in Sheridan’s army, then offered the name of a loyal Winchester schoolteacher, 24-year-old Rebecca Wright, he had met on a previous movement through the town. With the assistance of these two individuals, Sheridan had an opportunity to obtain information he needed about Early’s nearby forces.

On 16 September, after personally vetting Laws, Sheridan gave him a message written on tissue paper and wrapped in tinfoil with instructions and entreaties about the importance of secrecy and haste. Hiding the small pellet in his mouth, Laws crossed the Confederate lines and delivered it to Wright, informing her he would return later in the day for her response. Understandably anxious, Wright nevertheless responded with information shared by a wounded Confederate soldier who had visited her house the night before: the two Confederate divisions worrying Sheridan had been sent back to Lee in Richmond.

Sheridan wrote in his memoirs: “Miss Wright’s answer proved of more value to me than she anticipated, for it not only quieted the conflicting reports…, but was most important in showing positively that Kershaw was gone.” Consequently, on 19 September, Sheridan’s force advanced toward Winchester, crossing the Opequon Creek and engaging Early’s force of 15,000 east of town. By dusk, outnumbered nearly three to one, Early was forced to retreat and would be unable to recover in the closing months of the war.

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• Date Taken: 09.15.2023
• Date Posted: 09.15.2023 16:40
• Story ID: 453572
• Location: US